Echinacoside - Moligand™,10mM in DMSO , CAS No.82854-37-3

CAS: 82854-37-3 Cat. No.: E426143 Molecular Weight: 786.73 EC Number: 617-397-7

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

A12039 | s3783 | .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->3)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->6))-, 4-(3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE) | Echinacoside,(S) | HMS3885K04 | NCGC00091915-02 | AKOS0158971

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

A specialty product for proteomics research

Specifications

Synonyms

A12039 | s3783 | .BETA.-D-GLUCOPYRANOSIDE, 2-(3, 4-DIHYDROXYPHENYL)ETHYL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->3)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->6))-, 4-(3-(3, 4-DIHYDROXYPHENYL)-2-PROPENOATE) | Echinacoside, (S) | HMS3885K04 | NCGC00091915-02 | AKOS0158971

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Caffeic acid glycoside. Antiapoptotic agent. Stimulates proliferation and inhibits apoptosis via upregulation of TGF-β1 expression. Shows antiapoptotic and anti-inflammatory effects in vivo. Orally active.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
• IUPAC Name: [(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• InChIKey: FSBUXLDOLNLABB-ISAKITKMSA-N
• INCHI: 1S/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O
• Molecular Weight: 786.73
• Reaxy-Rn: 37848911
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37848911&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Oligosaccharides
• Alternative Parents: Cinnamic acid esters Coumaric acids and derivatives O-glycosyl compounds Tyrosols and derivatives Styrenes Catechols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Fatty acid esters Oxanes Enoate esters Secondary alcohols Polyols Acetals Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Organic oxides Carbonyl compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Oligosaccharide - Cinnamic acid or derivatives - Coumaric acid or derivatives - Hydroxycinnamic acid or derivatives - Cinnamic acid ester - Glycosyl compound - O-glycosyl compound - Tyrosol derivative - Catechol - Styrene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Fatty acid ester - Phenol - Monocyclic benzene moiety - Oxane - Benzenoid - Fatty acyl - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Secondary alcohol - Carboxylic acid ester - Polyol - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Oxacycle - Acetal - Carbonyl group - Primary alcohol - Alcohol - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
• External Descriptors: oligosaccharide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CXCL8 Tchem Interleukin-8 (642 Activities)

Discover Target: CXCL8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

Discover Target: ALOX15

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Lymphoblastoid cell (5959 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 786.700 g/mol
• XLogP3: -2.100
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 14
• Exact Mass: 786.258 Da
• Monoisotopic Mass: 786.258 Da
• Topological Polar Surface Area: 324.000 Ų
• Heavy Atom Count: 55
• Formal Charge: 0
• Complexity: 1230.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 15
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Yanfang Wu, Yindi Chu, Qinyu Yang, Mengjia Li, Miao Yu, Ruixue Deng, Kun Liu, Xinsheng Wang, Enguo Fan.  (2021)  Response surface methodology optimised solvothermal system enables an efficient extraction of echinacoside and oleuropein from Syringa pubescens Turcz.  PHYTOCHEMICAL ANALYSIS,  32  (6): (1074-1081).  [PMID:33837595] [10.1002/pca.3049]

2. Xinsheng Wang, Yanfang Wu, Jie Li, Aoxiang Wang, Guangyao Li, Xueli Ren, Weiping Yin.  (2020)  Ultrasound-assisted deep eutectic solvent extraction of echinacoside and oleuropein from Syringa pubescens Turcz..  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2020.112442]

3. Min Chen, Xiaodong Wang, Bo Hu, Jian Zhou, Xin Wang, Wei Wei, Hua Zhou.  (2018)  Protective effects of echinacoside against anoxia/reperfusion injury in H9c2 cells via up-regulating p-AKT and SLC8A3.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:29763795] [10.1016/j.biopha.2018.04.188]

4. Lu Jianrao, Yi Yang, Pan Ronghua, Zhang Chuanfu, Han Haiyan, Chen Jie, Liu Wenrui.  (2017)  Berberine protects HK-2 cells from hypoxia/reoxygenation induced apoptosis via inhibiting SPHK1 expression.  Journal of Natural Medicines,  72  (2): (390-398).  [PMID:29260413] [10.1007/s11418-017-1152-z]

5. Wang Guoyu, Han Yang, Zhuang Juhua, Mai Zhongchao, Xia Wei, Ye Ying.  (2024)  Echinacoside inhibits hepatocellular carcinoma progression by targeting the miR-30c-5p/FOXD1/KLF12 axis.  TECHNOLOGY AND HEALTH CARE,      [PMID:39269873] [10.3233/THC-241449]

6. Zi-Chen Zhang, Yan-Fang Wu, Jian-Sheng Xiong, Xin-Yi Guan, Su-Ya Zhang, Xin-Sheng Wang.  (2024)  Purification of Phenylethanoid Glycosides From Syringa pubescens Turcz. via Macroporous Resins and Comparison of Biological Activity.  Separation Science Plus,  8  (1): (e202400247).  [PMID:] [10.1002/sscp.202400247]

7. Wei-fang Song, Sheng-nan Li, Rui-xin Yao, Qiu-yan Jiang, Ting Shi, Dan-dan Fan, Hai-juan Zhang, Wen-hui Zhang, Rui-jun Wang.  (2025)  Echinacoside Alleviates Non-Alcoholic Fatty Liver Disease in Rats: Potential Involvement of AMPK Pathway and Autophagy.  Chemical Biology & Drug Design,  105  (4): (e70097).  [PMID:40205786] [10.1111/cbdd.70097]

8. Yang Han, Junyong Fan, Wei Xia, Xiao Dong, Ying Ye.  (2025)  Folic acid-functionalized PLGA nanomedicines encapsulating echinacoside for liver cancer therapy.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,      [PMID:40446750] [10.1016/j.bbrc.2025.152049]